DE2830927A1 - Acylphosphinoxidverbindungen und ihre verwendung - Google Patents
Acylphosphinoxidverbindungen und ihre verwendungInfo
- Publication number
- DE2830927A1 DE2830927A1 DE19782830927 DE2830927A DE2830927A1 DE 2830927 A1 DE2830927 A1 DE 2830927A1 DE 19782830927 DE19782830927 DE 19782830927 DE 2830927 A DE2830927 A DE 2830927A DE 2830927 A1 DE2830927 A1 DE 2830927A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- parts
- carbon atoms
- acid
- basf aktiengesellschaft
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 0.000 claims 1
- -1 benzoin ethers Chemical class 0.000 description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
- 238000004458 analytical method Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- OAADXJFIBNEPLY-UHFFFAOYSA-N methoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OC)C1=CC=CC=C1 OAADXJFIBNEPLY-UHFFFAOYSA-N 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- LMZLQYYLELWCCW-UHFFFAOYSA-N dimethoxy(phenyl)phosphane Chemical compound COP(OC)C1=CC=CC=C1 LMZLQYYLELWCCW-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- OVSFXKCTADOYFM-UHFFFAOYSA-N benzhydryloxyphosphane Chemical compound C=1C=CC=CC=1C(OP)C1=CC=CC=C1 OVSFXKCTADOYFM-UHFFFAOYSA-N 0.000 description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- LDNCAOOMUMJYTN-UHFFFAOYSA-N phenyl-di(propan-2-yloxy)phosphane Chemical compound CC(C)OP(OC(C)C)C1=CC=CC=C1 LDNCAOOMUMJYTN-UHFFFAOYSA-N 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920006305 unsaturated polyester Polymers 0.000 description 3
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000003678 scratch resistant effect Effects 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- VVZUXOSFQDGMIH-UHFFFAOYSA-N 1-[methoxy(phenyl)phosphoryl]prop-2-en-1-one Chemical compound C=CC(=O)P(=O)(OC)C1=CC=CC=C1 VVZUXOSFQDGMIH-UHFFFAOYSA-N 0.000 description 1
- RPMLFEYJLCDKFM-UHFFFAOYSA-N 1-diethoxyphosphoryl-2,2-dimethylpropan-1-one Chemical compound CCOP(=O)(OCC)C(=O)C(C)(C)C RPMLFEYJLCDKFM-UHFFFAOYSA-N 0.000 description 1
- ZFIVBGXETFWLQL-UHFFFAOYSA-N 1-diphenylphosphoryl-2-ethyl-2-methylhexan-1-one Chemical compound C=1C=CC=CC=1P(=O)(C(=O)C(C)(CC)CCCC)C1=CC=CC=C1 ZFIVBGXETFWLQL-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- DSKGWFQMJHBHRT-UHFFFAOYSA-N 2,2-diethoxyacetamide Chemical compound CCOC(C(N)=O)OCC DSKGWFQMJHBHRT-UHFFFAOYSA-N 0.000 description 1
- QDJHMOSPJGJYPX-UHFFFAOYSA-N 2,2-dimethyl-1-[phenyl(propan-2-yloxy)phosphoryl]propan-1-one Chemical compound CC(C)OP(=O)(C(=O)C(C)(C)C)C1=CC=CC=C1 QDJHMOSPJGJYPX-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- MPCHQYWZAVTABQ-UHFFFAOYSA-N 2-(chloromethyl)naphthalene Chemical compound C1=CC=CC2=CC(CCl)=CC=C21 MPCHQYWZAVTABQ-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- DVYVBENBIMEAJZ-UHFFFAOYSA-N 2-(n-methylanilino)acetic acid Chemical compound OC(=O)CN(C)C1=CC=CC=C1 DVYVBENBIMEAJZ-UHFFFAOYSA-N 0.000 description 1
- ROGMVTGBFVTARY-UHFFFAOYSA-N 2-ethyl-1-[methoxy(phenyl)phosphoryl]hexan-1-one Chemical compound CCCCC(CC)C(=O)P(=O)(OC)C1=CC=CC=C1 ROGMVTGBFVTARY-UHFFFAOYSA-N 0.000 description 1
- KQMKJGXDDZOKPF-UHFFFAOYSA-N 2-ethyl-2-methylhexanoyl chloride Chemical compound CCCCC(C)(CC)C(Cl)=O KQMKJGXDDZOKPF-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SYEZSRFAWVLENF-UHFFFAOYSA-N 3,3-dimethyloctanoyl chloride Chemical compound CCCCCC(C)(C)CC(Cl)=O SYEZSRFAWVLENF-UHFFFAOYSA-N 0.000 description 1
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- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
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- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
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- PNLXQFOXOPGOGI-UHFFFAOYSA-N 4-tert-butylbenzoic acid;hydrochloride Chemical compound Cl.CC(C)(C)C1=CC=C(C(O)=O)C=C1 PNLXQFOXOPGOGI-UHFFFAOYSA-N 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- OSPMKIFLYSESOG-UHFFFAOYSA-N butyl(dimethoxy)phosphane Chemical compound CCCCP(OC)OC OSPMKIFLYSESOG-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 150000001805 chlorine compounds Chemical class 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
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- 239000013256 coordination polymer Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- YBAAIJIDIRQVLY-UHFFFAOYSA-N dibutoxy(phenyl)phosphane Chemical compound CCCCOP(OCCCC)C1=CC=CC=C1 YBAAIJIDIRQVLY-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- ZXMSTCRBSAVFDO-UHFFFAOYSA-N dimethoxy(methyl)phosphane Chemical compound COP(C)OC ZXMSTCRBSAVFDO-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- QCASTONPZLJEOJ-UHFFFAOYSA-N diphenyl(propan-2-yloxy)phosphane Chemical compound C=1C=CC=CC=1P(OC(C)C)C1=CC=CC=C1 QCASTONPZLJEOJ-UHFFFAOYSA-N 0.000 description 1
- UTZDKCFZGDSBGI-UHFFFAOYSA-N diphenylphosphoryl-(1-methylcyclohexyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1(C)CCCCC1 UTZDKCFZGDSBGI-UHFFFAOYSA-N 0.000 description 1
- HZWAUDKTZOUQPD-UHFFFAOYSA-N diphenylphosphoryl-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 HZWAUDKTZOUQPD-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ODXKYOFRPVSRTK-UHFFFAOYSA-N methoxy(dimethyl)phosphane Chemical compound COP(C)C ODXKYOFRPVSRTK-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- BCDIWLCKOCHCIH-UHFFFAOYSA-M methylphosphinate Chemical compound CP([O-])=O BCDIWLCKOCHCIH-UHFFFAOYSA-M 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002872 norbornadienyl group Chemical group C12=C(C=C(CC1)C2)* 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3247—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782830927 DE2830927A1 (de) | 1978-07-14 | 1978-07-14 | Acylphosphinoxidverbindungen und ihre verwendung |
| DE7979102347T DE2965566D1 (en) | 1978-07-14 | 1979-07-09 | Acylphosphinoxide compounds, their preparation and their use |
| EP79102347A EP0007508B1 (de) | 1978-07-14 | 1979-07-09 | Acylphosphinoxidverbindungen, ihre Herstellung und ihre Verwendung |
| ES482450A ES482450A1 (es) | 1978-07-14 | 1979-07-12 | Procedimiento para la obtencion de compuestos de oxido de acilfosfina. |
| FI792196A FI68241C (fi) | 1978-07-14 | 1979-07-12 | Fotopolymeriserbar massa |
| DK295979A DK171353B1 (da) | 1978-07-14 | 1979-07-13 | Acylphosphinoxidforbindelser til anvendelse som fotoinitiatorer |
| NO792333A NO792333L (no) | 1978-07-14 | 1979-07-13 | Acylfosfinoksydforbindelser og anvendelse av slike i fotopolymeriserbar oppmerkingsmasse |
| JP8833679A JPS5515471A (en) | 1978-07-14 | 1979-07-13 | Acylphosphine oxide compound*its manufacture and its use |
| CA000331829A CA1138877A (en) | 1978-07-14 | 1979-07-13 | Acylphosphine oxide compound and their use |
| US06/148,221 US4324744A (en) | 1978-07-14 | 1980-05-09 | Acylphosphine oxide compounds |
| DK436682A DK162722C (da) | 1978-07-14 | 1982-10-01 | Fotopolymeriserbart registreringsmateriale |
| DK436582A DK172228B1 (da) | 1978-07-14 | 1982-10-01 | Fotopolymeriserbar masse til fotopolymeriserbare overtræksmidler, lakker og trykfarver |
| FI840240A FI69085C (fi) | 1978-07-14 | 1984-01-20 | Fotopolymeriserbar registreringsmassa isynnerhet foer framstaellning av tryckplattor och reliefformar |
| NO84841029A NO160215C (no) | 1978-07-14 | 1984-03-16 | Fotopolymeriserbar oppmerkingsmasse samt fremgangsmaate for fremstilling av relieff-former. |
| NO841028A NO160214C (no) | 1978-07-14 | 1984-03-16 | Fotopolymeriserbare masser. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782830927 DE2830927A1 (de) | 1978-07-14 | 1978-07-14 | Acylphosphinoxidverbindungen und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2830927A1 true DE2830927A1 (de) | 1980-01-31 |
Family
ID=6044344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782830927 Withdrawn DE2830927A1 (de) | 1978-07-14 | 1978-07-14 | Acylphosphinoxidverbindungen und ihre verwendung |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4324744A (cs) |
| JP (1) | JPS5515471A (cs) |
| CA (1) | CA1138877A (cs) |
| DE (1) | DE2830927A1 (cs) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0047902A3 (en) * | 1980-09-15 | 1982-09-29 | Basf Aktiengesellschaft | Acylphosphinesulfide compounds, process for their preparation and their use |
| EP0057474A3 (en) * | 1979-03-14 | 1982-10-13 | Basf Aktiengesellschaft | Acylphosphine oxde compounds, their preparation and use |
| EP0062839A1 (de) * | 1981-04-09 | 1982-10-20 | BASF Aktiengesellschaft | Acylphosphinverbindungen und ihre Verwendung |
| DE3139984A1 (de) * | 1981-10-08 | 1983-04-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von acylphosphinoxiden |
| US4447520A (en) * | 1981-08-24 | 1984-05-08 | Basf Aktiengesellschaft | Acylphosphine oxides and their use |
| DE3443221A1 (de) * | 1984-11-27 | 1986-06-05 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Bisacylphosphinoxide, ihre herstellung und verwendung |
| DE4025386A1 (de) * | 1990-08-10 | 1992-02-27 | Herberts Gmbh | Verfahren zur haertung von radikalisch polymerisierbaren massen, ueberzuegen und druckfarben, neue carboxyphosphanoxide und deren verwendung als photoinitiatoren |
| US5750590A (en) * | 1995-02-22 | 1998-05-12 | Heraeus Kulzer Gmbh | Polymerizable material |
| US6114408A (en) * | 1998-02-06 | 2000-09-05 | American Dental Association Health Foundation | Single-solution adhesive resin formulations |
| EP2065890A2 (en) | 2007-11-30 | 2009-06-03 | FUJIFILM Corporation | Optical recording composition and holographic recording medium |
| WO2010110055A1 (ja) | 2009-03-23 | 2010-09-30 | 富士フイルム株式会社 | 接合型レンズ用硬化性樹脂組成物、撮像レンズ、及び、撮像レンズの製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4757141A (en) * | 1985-08-26 | 1988-07-12 | Applied Biosystems, Incorporated | Amino-derivatized phosphite and phosphate linking agents, phosphoramidite precursors, and useful conjugates thereof |
| DE3738567A1 (de) * | 1987-03-12 | 1988-09-22 | Merck Patent Gmbh | Coreaktive fotoinitiatoren |
| JP2615180B2 (ja) * | 1987-05-01 | 1997-05-28 | 三菱レイヨン株式会社 | 注型重合用活性光線硬化性組成物 |
| JPH0655654B2 (ja) * | 1987-07-21 | 1994-07-27 | 株式会社クラレ | 光硬化性歯冠材料および該歯冠材料を用いる歯冠成形法 |
| EP0304782B1 (de) * | 1987-08-24 | 1993-12-01 | Hoechst Aktiengesellschaft | Neue 6-Acyl-(6H)-dibenz[c,e] [1,2]oxaphosphorin-6-oxyde, ihre Herstellung und Verwendung als Photoinitiatoren |
| DE3736180A1 (de) * | 1987-10-26 | 1989-05-03 | Basf Ag | Verfahren zum verschliessen und/oder abdichten von oeffnungen, hohl- oder zwischenraeumen bei auf formzylindern aufgebrachten druckplatten |
| DE3837569A1 (de) * | 1988-11-04 | 1990-05-10 | Espe Stiftung | Mit sichtbarem licht aushaertbare dentalmassen |
| US5218009A (en) * | 1989-08-04 | 1993-06-08 | Ciba-Geigy Corporation | Mono- and di-acylphosphine oxides |
| JPH03174472A (ja) * | 1989-11-24 | 1991-07-29 | Dainippon Toryo Co Ltd | 紫外線硬化型被覆組成物 |
| JPH03192163A (ja) * | 1989-12-21 | 1991-08-22 | Dainippon Toryo Co Ltd | 紫外線硬化型塗料組成物 |
| EP0560724B1 (de) * | 1992-03-11 | 1997-09-24 | Ciba SC Holding AG | Benzoyl substituierte Phosphabicycloalkane und -sulfide als Photoinitiatoren |
| US5352713A (en) * | 1992-04-01 | 1994-10-04 | Allied-Signal Inc. | Free radical co-polymerization of acrylates and vinyl ethers |
| DE4230555A1 (de) * | 1992-09-12 | 1994-03-17 | Basf Ag | Verfahren zur Herstellung von alpha-Carbonylphosphinoxiden |
| DE4240964A1 (de) * | 1992-12-05 | 1994-06-09 | Basf Ag | Arenbisphosphinoxide |
| US5906490A (en) * | 1994-06-09 | 1999-05-25 | Ceramco Inc. | Dental product, shading kit and method |
| MX9701734A (es) * | 1994-09-08 | 1997-06-28 | Ciba Sc Holding Ag | Novedosos oxidos de acilfosfina. |
| US6075065A (en) * | 1996-12-20 | 2000-06-13 | Takeda Chemical Industries, Ltd. | Photocurable resin composition and a method for producing the same |
| US5891931A (en) * | 1997-08-07 | 1999-04-06 | Alcon Laboratories, Inc. | Method of preparing foldable high refractive index acrylic ophthalmic device materials |
| US6015842A (en) * | 1997-08-07 | 2000-01-18 | Alcon Laboratories, Inc. | Method of preparing foldable hydrophilic ophthalmic device materials |
| DE69907431T2 (de) | 1998-03-13 | 2004-04-08 | Akzo Nobel N.V. | Nicht-wässriges überzugsmittel auf basis eines lufttrocknenden alkydharzes und eines photoinitiators |
| SE9904080D0 (sv) | 1998-12-03 | 1999-11-11 | Ciba Sc Holding Ag | Fotoinitiatorberedning |
| GB2365430B (en) * | 2000-06-08 | 2002-08-28 | Ciba Sc Holding Ag | Acylphosphine photoinitiators and intermediates |
| DE10206117A1 (de) * | 2002-02-13 | 2003-08-14 | Basf Ag | Acyl- und Bisacylphosphinderivate |
| DE60322388D1 (de) * | 2002-06-11 | 2008-09-04 | Ciba Holding Inc | Multimere formen von mono- und bis-acylphosphinoxiden |
| JP4485117B2 (ja) * | 2002-06-27 | 2010-06-16 | 日東電工株式会社 | 保護剥離用フィルム |
| US7134875B2 (en) * | 2002-06-28 | 2006-11-14 | 3M Innovative Properties Company | Processes for forming dental materials and device |
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| US20040122126A1 (en) * | 2002-12-20 | 2004-06-24 | Dong Wu | Free-radical initiator systems containing enzymes, compositions, and methods |
| US20040206932A1 (en) * | 2002-12-30 | 2004-10-21 | Abuelyaman Ahmed S. | Compositions including polymerizable bisphosphonic acids and methods |
| DE10315671A1 (de) * | 2003-04-04 | 2004-10-14 | Basf Ag | Verfahren zur Herstellung von Acylphosphinoxid-Feststoffen |
| CN1859892B (zh) * | 2003-08-12 | 2012-05-16 | 3M创新有限公司 | 自蚀牙科组合物和方法 |
| RU2396287C2 (ru) * | 2004-04-15 | 2010-08-10 | Циба Спешиалти Кемикэлз Холдинг Инк. | Способ фотохимического отверждения светоизлучающими диодами |
| US7090722B2 (en) | 2004-05-17 | 2006-08-15 | 3M Innovative Properties Company | Acid-reactive dental fillers, compositions, and methods |
| US7156911B2 (en) | 2004-05-17 | 2007-01-02 | 3M Innovative Properties Company | Dental compositions containing nanofillers and related methods |
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| AU2005269869B2 (en) * | 2004-07-08 | 2011-12-01 | 3M Innovative Properties Company | Dental methods, compositions, and kits including acid-sensitive dyes |
| WO2006020760A1 (en) * | 2004-08-11 | 2006-02-23 | 3M Innovative Properties Company | Self-adhesive compositions including a plurality of acidic compounds |
| DE602004022551D1 (de) * | 2004-09-24 | 2009-09-24 | 3M Espe Ag | Dentalklebstoffzusammensetzung |
| ATE480214T1 (de) | 2004-11-16 | 2010-09-15 | 3M Innovative Properties Co | Dentalfüllstoffe, verfahren, zusammensetzungen mit einem caseinat |
| EP1819313B1 (en) * | 2004-11-16 | 2010-12-29 | 3M Innovative Properties Company | Dental fillers and compositions including phosphate salts |
| ATE526935T1 (de) | 2004-11-16 | 2011-10-15 | 3M Innovative Properties Co | Dentale zusammensetzungen mit calziumphosphor- freisetzendem glas |
| CA2587556A1 (en) | 2004-11-16 | 2006-05-26 | 3M Innovative Properties Company | Dental fillers including a phosphorus containing surface treatment, and compositions and methods thereof |
| EP1851276B1 (de) | 2005-02-10 | 2017-01-25 | BASF Coatings GmbH | Verfahren zum aufbringen chromfreier korrosionsschutzschichten enthaltend dithiophosphinsäuren und/oder deren salzen |
| DE102005010327A1 (de) * | 2005-03-03 | 2006-09-07 | Basf Ag | Ratikalisch härtbare Beschichtungsmassen |
| US20060205838A1 (en) * | 2005-03-10 | 2006-09-14 | Velamakanni Bhaskar V | Hardenable antimicrobial dental compositions and methods |
| US20060204452A1 (en) * | 2005-03-10 | 2006-09-14 | Velamakanni Bhaskar V | Antimicrobial film-forming dental compositions and methods |
| CN102512329A (zh) | 2005-05-09 | 2012-06-27 | 3M创新有限公司 | 含有杂化单体的牙科组合物 |
| ATE473723T1 (de) * | 2005-08-05 | 2010-07-15 | 3M Espe Ag | Dentalzusammensetzungen mit einem oberflächenmodifizierten füllstoff |
| US7495054B2 (en) * | 2005-09-19 | 2009-02-24 | 3M Innovative Properties Company | Curable compositions containing dithiane monomers |
| EP1787627A1 (en) * | 2005-11-17 | 2007-05-23 | 3M Innovative Properties Company | Anti-microbial dental impression material |
| US7896650B2 (en) * | 2005-12-20 | 2011-03-01 | 3M Innovative Properties Company | Dental compositions including radiation-to-heat converters, and the use thereof |
| US8026296B2 (en) | 2005-12-20 | 2011-09-27 | 3M Innovative Properties Company | Dental compositions including a thermally labile component, and the use thereof |
| US20070142498A1 (en) * | 2005-12-20 | 2007-06-21 | Brennan Joan V | Dental compositions including thermally responsive additives, and the use thereof |
| US7776940B2 (en) * | 2005-12-20 | 2010-08-17 | 3M Innovative Properties Company | Methods for reducing bond strengths, dental compositions, and the use thereof |
| JP5271089B2 (ja) * | 2005-12-29 | 2013-08-21 | スリーエム イノベイティブ プロパティズ カンパニー | 歯科用組成物及び多環式芳香族構成要素を有する開始剤系 |
| JP2009522279A (ja) * | 2005-12-29 | 2009-06-11 | スリーエム イノベイティブ プロパティズ カンパニー | 水スカベンジャーを有する歯科用組成物 |
| WO2007079166A1 (en) * | 2005-12-29 | 2007-07-12 | 3M Innovative Properties Company | Dental compositions with surface-treated filler for shelf stability |
| EP2239275B1 (en) | 2006-05-31 | 2011-11-09 | 3M Innovative Properties Company | Polymerizable compositions containing salts of barbituric acid derivates |
| WO2008033911A2 (en) | 2006-09-13 | 2008-03-20 | 3M Innovative Properties Company | Dental compositions including organogelators, products, and methods |
| US20080096150A1 (en) | 2006-10-23 | 2008-04-24 | 3M Innovative Properties Company | Dental articles, methods, and kits including a compressible material |
| US9539065B2 (en) | 2006-10-23 | 2017-01-10 | 3M Innovative Properties Company | Assemblies, methods, and kits including a compressible material |
| KR101148660B1 (ko) * | 2006-11-01 | 2012-05-22 | 후지쯔 가부시끼가이샤 | 무선 통신 장치 및 무선 통신 방법 |
| JP5507256B2 (ja) * | 2006-12-13 | 2014-05-28 | スリーエム イノベイティブ プロパティズ カンパニー | 酸性成分及び光退色性染料を有する歯科用組成物の使用方法 |
| US8263681B2 (en) * | 2006-12-28 | 2012-09-11 | 3M Innovative Properties Company | Dental compositions with natural tooth fluorescence |
| EP2109436B1 (en) * | 2006-12-28 | 2012-01-25 | 3M Innovative Properties Company | Adhesive composition for hard tissue |
| JP5512280B2 (ja) * | 2006-12-28 | 2014-06-04 | スリーエム イノベイティブ プロパティズ カンパニー | 歯科充填剤及び方法 |
| US20100021869A1 (en) * | 2006-12-28 | 2010-01-28 | Abuelyaman Ahmed S | (meth)acryloyl-containing materials, compositions, and methods |
| US7985785B2 (en) | 2007-01-15 | 2011-07-26 | Fujifilm Corporation | Ink composition and inkjet recording method using the same |
| EP1958994B1 (en) | 2007-01-31 | 2010-12-08 | FUJIFILM Corporation | Ink set for inkjet recording and inkjet recording method |
| JP5227521B2 (ja) | 2007-02-26 | 2013-07-03 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、インクセット |
| JP5243072B2 (ja) | 2007-03-30 | 2013-07-24 | 富士フイルム株式会社 | インク組成物、並びに、それを用いた画像記録方法及び画像記録物 |
| JP5306681B2 (ja) | 2007-03-30 | 2013-10-02 | 富士フイルム株式会社 | 重合性化合物、重合体、インク組成物、印刷物及びインクジェット記録方法 |
| JP4601009B2 (ja) | 2007-03-30 | 2010-12-22 | 富士フイルム株式会社 | インクジェット記録用インクセット及びインクジェット記録方法 |
| JP5255369B2 (ja) | 2007-09-25 | 2013-08-07 | 富士フイルム株式会社 | 光硬化性コーティング組成物、オーバープリント及びその製造方法 |
| US8076393B2 (en) | 2007-09-26 | 2011-12-13 | Fujifilm Corporation | Ink composition, inkjet recording method, and printed material |
| JP5148235B2 (ja) | 2007-09-28 | 2013-02-20 | 富士フイルム株式会社 | インク組成物 |
| US8129447B2 (en) | 2007-09-28 | 2012-03-06 | Fujifilm Corporation | Ink composition and inkjet recording method using the same |
| JP5236238B2 (ja) | 2007-09-28 | 2013-07-17 | 富士フイルム株式会社 | インクジェット記録用ホワイトインク組成物 |
| JP5227560B2 (ja) | 2007-09-28 | 2013-07-03 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物の製造方法 |
| WO2009045752A2 (en) | 2007-10-01 | 2009-04-09 | 3M Innovative Properties Company | Orthodontic composition with polymeric fillers |
| US20090142672A1 (en) * | 2007-11-30 | 2009-06-04 | Fujifilm Corporation | Optical recording composition and holographic recording medium |
| JP2011505973A (ja) * | 2007-12-13 | 2011-03-03 | スリーエム イノベイティブ プロパティズ カンパニー | 部分的に硬化した組成物を有する歯科矯正用物品並びにその使用及び製造方法 |
| EP2229130A2 (en) * | 2007-12-13 | 2010-09-22 | 3M Innovative Properties Company | Remineralizing compositions and methods |
| JP5457636B2 (ja) | 2008-01-22 | 2014-04-02 | 富士フイルム株式会社 | 光硬化性組成物、光硬化性インク組成物、光硬化物の製造方法、及び、インクジェット記録方法 |
| JP5254632B2 (ja) | 2008-02-07 | 2013-08-07 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物 |
| JP4914862B2 (ja) | 2008-03-26 | 2012-04-11 | 富士フイルム株式会社 | インクジェット記録方法、及び、インクジェット記録装置 |
| JP5414367B2 (ja) | 2008-06-02 | 2014-02-12 | 富士フイルム株式会社 | 顔料分散物及びそれを用いたインク組成物 |
| EP2133063A1 (en) * | 2008-06-10 | 2009-12-16 | 3M Innovative Properties Company | Initiator system with biphenylene derivates, method of production and use thereof |
| US8378002B2 (en) | 2008-07-16 | 2013-02-19 | Fujifilm Corporation | Aqueous ink composition, aqueous ink composition for inkjet recording, and inkjet recording method |
| EP2331046A2 (en) * | 2008-09-04 | 2011-06-15 | 3M Innovative Properties Company | Dental composition comprising biphenyl di(meth)acrylate monomer |
| US20110171591A1 (en) * | 2008-09-30 | 2011-07-14 | Amos David T | Orthodontic composition with heat modified minerals |
| CN102245154B (zh) | 2008-10-15 | 2014-09-03 | 3M创新有限公司 | 具有荧光颜料的牙科用组合物 |
| EP2376573B1 (en) * | 2008-10-22 | 2019-12-18 | 3M Innovative Properties Company | Dental composition comprising biphenyl di(meth)acrylate monomer comprising urethane moieties |
| KR101648996B1 (ko) | 2008-11-03 | 2016-08-17 | 바스프 에스이 | 광개시제 혼합물 |
| JP5344892B2 (ja) | 2008-11-27 | 2013-11-20 | 富士フイルム株式会社 | インクジェット用インク組成物、及びインクジェット記録方法 |
| US8790707B2 (en) * | 2008-12-11 | 2014-07-29 | 3M Innovative Properties Company | Surface-treated calcium phosphate particles suitable for oral care and dental compositions |
| JP2010180330A (ja) | 2009-02-05 | 2010-08-19 | Fujifilm Corp | 非水系インク、インクセット、画像記録方法、画像記録装置、および記録物 |
| JP5350827B2 (ja) | 2009-02-09 | 2013-11-27 | 富士フイルム株式会社 | インク組成物、及び、インクジェット記録方法 |
| JP5349097B2 (ja) | 2009-03-19 | 2013-11-20 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物の製造方法 |
| JP2010229284A (ja) | 2009-03-27 | 2010-10-14 | Fujifilm Corp | 光硬化性組成物 |
| JP5405174B2 (ja) | 2009-03-30 | 2014-02-05 | 富士フイルム株式会社 | インク組成物 |
| JP5424764B2 (ja) | 2009-07-28 | 2014-02-26 | 富士フイルム株式会社 | 顔料分散物、インク組成物、及び、インクジェット記録方法 |
| JP2011068783A (ja) | 2009-09-25 | 2011-04-07 | Fujifilm Corp | インク組成物、及び、インクジェット記録方法 |
| JP5530141B2 (ja) | 2009-09-29 | 2014-06-25 | 富士フイルム株式会社 | インク組成物及びインクジェット記録方法 |
| WO2011087832A1 (en) | 2009-12-22 | 2011-07-21 | 3M Innovative Properties Company | Dental compositions, mill blocks, and methods |
| JP2012031388A (ja) | 2010-05-19 | 2012-02-16 | Fujifilm Corp | 印刷方法、オーバープリントの作製方法、ラミネート加工方法、発光ダイオード硬化性コーティング組成物、及び、発光ダイオード硬化性インク組成物 |
| WO2012027091A1 (en) | 2010-08-11 | 2012-03-01 | 3M Innovative Properties Company | Dental articles including a ceramic and microparticle coating and method of making the same |
| WO2012021442A1 (en) | 2010-08-11 | 2012-02-16 | 3M Innovative Properties Company | Coated dental crows and method of making the same |
| EP2603160A2 (en) | 2010-08-11 | 2013-06-19 | 3M Innovative Properties Company | Polymer coated dental articles and method of making the same |
| WO2012021438A1 (en) | 2010-08-11 | 2012-02-16 | 3M Innovative Properties Company | Aesthetic and abrasion resistant coated dental articles and methods of making the same |
| EP2658469B1 (en) | 2010-12-30 | 2019-11-27 | 3M Innovative Properties Company | Bondable dental assemblies and methods including a compressible material |
| US8816211B2 (en) | 2011-02-14 | 2014-08-26 | Eastman Kodak Company | Articles with photocurable and photocured compositions |
| US20120207935A1 (en) | 2011-02-14 | 2012-08-16 | Deepak Shukla | Photocurable inks and methods of use |
| US20120208914A1 (en) | 2011-02-14 | 2012-08-16 | Deepak Shukla | Photoinitiator compositions and uses |
| EP2688508A1 (en) | 2011-03-24 | 2014-01-29 | 3M Innovative Properties Company | Dental adhesive comprising a coated polymeric component |
| JP5750069B2 (ja) | 2011-03-24 | 2015-07-15 | 富士フイルム株式会社 | 液晶配向促進剤、液晶組成物、高分子材料およびフィルム |
| JP5774518B2 (ja) | 2011-07-27 | 2015-09-09 | 富士フイルム株式会社 | 化合物、ヘイズ低下剤、液晶組成物、高分子材料およびフィルム |
| JP5566979B2 (ja) | 2011-09-22 | 2014-08-06 | 富士フイルム株式会社 | インクジェット記録用インク組成物、インクパック、及び、インクジェット記録方法 |
| JP5958803B2 (ja) | 2012-03-28 | 2016-08-02 | 富士フイルム株式会社 | 活性光線硬化型インクジェットインク組成物及びその製造方法、インクジェット記録方法、並びに、印刷物 |
| JP5827161B2 (ja) | 2012-03-28 | 2015-12-02 | 富士フイルム株式会社 | コレステリック液晶性混合物、フィルム、赤外反射板、積層体および合わせガラス |
| CN104519863A (zh) | 2012-06-04 | 2015-04-15 | 欧莱雅 | 用于采用uv-led对可自由基聚合的树脂进行光固化而产生无粘性表面的快速固化化妆品组合物 |
| JP5752652B2 (ja) | 2012-08-29 | 2015-07-22 | 富士フイルム株式会社 | インクジェットインク組成物及びその製造方法、インクジェット記録方法、並びに、顔料分散物及びその製造方法 |
| JP6016768B2 (ja) * | 2013-02-21 | 2016-10-26 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、及び、高分子開始剤 |
| JP5980702B2 (ja) | 2013-03-07 | 2016-08-31 | 富士フイルム株式会社 | インクジェットインク組成物、インクジェット記録方法、及び、成型印刷物の製造方法 |
| JP5939640B2 (ja) | 2013-03-08 | 2016-06-22 | 富士フイルム株式会社 | 多層構成物、及び、多層構成物の製造方法 |
| JP5939644B2 (ja) | 2013-08-30 | 2016-06-22 | 富士フイルム株式会社 | 画像形成方法、インモールド成型品の製造方法、及び、インクセット |
| JP6656146B2 (ja) | 2013-10-04 | 2020-03-04 | スリーエム イノベイティブ プロパティズ カンパニー | 歯科用ミルブランク |
| JP6169545B2 (ja) | 2014-09-09 | 2017-07-26 | 富士フイルム株式会社 | 重合性組成物、インクジェット記録用インク組成物、インクジェット記録方法、及び記録物 |
| JP6086888B2 (ja) | 2014-09-26 | 2017-03-01 | 富士フイルム株式会社 | インクジェット記録用インク組成物、インクジェット記録方法、及び記録物 |
| JP6169548B2 (ja) | 2014-09-26 | 2017-07-26 | 富士フイルム株式会社 | 重合性組成物、インクジェット記録用インク組成物、インクジェット記録方法、及び記録物 |
| US9649272B2 (en) | 2014-10-13 | 2017-05-16 | L'oréal | Latex nail compositions having low amounts of photo-initiator |
| US9820931B2 (en) | 2014-10-13 | 2017-11-21 | L'oreal | Latex nail compositions having low amounts of photo-initiator |
| US9636293B2 (en) | 2014-10-13 | 2017-05-02 | L'oréal | Latex nail compositions having low amounts of photo-initiator |
| US10369086B2 (en) | 2015-03-05 | 2019-08-06 | 3M Innovative Properties Company | Composite material having ceramic fibers |
| EP3294780A4 (en) | 2015-06-08 | 2018-11-21 | DSM IP Assets B.V. | Liquid, hybrid uv/vis radiation curable resin compositions for additive fabrication |
| EP3106146A1 (en) * | 2015-06-15 | 2016-12-21 | Dentsply DeTrey GmbH | Aqueous dental glass ionomer composition |
| BR112018000244B8 (pt) * | 2015-07-06 | 2022-09-06 | Bluestar Silicones France | Itens autoadesivos de camadas múltiplas, processo para a preparação de um item autoadesivo de camadas múltiplas, composição c de silicone curável, substrato, e usos de um item autoadesivo de camadas múltiplas e de um substrato |
| EP3141567B1 (en) | 2015-09-09 | 2019-08-28 | DENTSPLY DETREY GmbH | Polymerizable polyacidic polymer |
| JP6880416B2 (ja) | 2015-10-01 | 2021-06-02 | ディーエスエム アイピー アセッツ ビー.ブイ.Dsm Ip Assets B.V. | 付加造形用液状ハイブリッドUV/vis線硬化性樹脂組成物 |
| JP6563028B2 (ja) | 2015-11-20 | 2019-08-21 | 富士フイルム株式会社 | 光重合開始剤及びその製造方法、重合性組成物、インクジェット記録方法、並びに、アシルホスフィンオキシド化合物 |
| EP3231411B1 (en) | 2016-04-15 | 2021-11-10 | DENTSPLY DETREY GmbH | Aqueous dental glass ionomer composition |
| EP3231412A3 (en) | 2016-04-15 | 2017-10-25 | DENTSPLY DETREY GmbH | Aqueous dental glass ionomer composition |
| EP3246002A1 (en) | 2016-05-20 | 2017-11-22 | DENTSPLY DETREY GmbH | Dental composition |
| EP3263089A1 (en) | 2016-06-30 | 2018-01-03 | Dentsply DeTrey GmbH | Dental composition comprising a dental filler containing a structural filler and silanated glass flakes |
| EP3300714A1 (en) | 2016-09-30 | 2018-04-04 | DENTSPLY DETREY GmbH | Dental composition |
| WO2018084076A1 (ja) | 2016-11-04 | 2018-05-11 | 富士フイルム株式会社 | ウインドシールドガラス、ヘッドアップディスプレイシステム、およびハーフミラーフィルム |
| EP3336092A1 (en) | 2016-12-14 | 2018-06-20 | DENTSPLY DETREY GmbH | Dental composition |
| EP3335689B1 (en) | 2016-12-14 | 2025-03-19 | DENTSPLY DETREY GmbH | Dental composition |
| EP3338757A1 (en) | 2016-12-20 | 2018-06-27 | Dentsply DeTrey GmbH | Direct dental filling composition |
| EP3339335A1 (en) | 2016-12-22 | 2018-06-27 | Dentsply DeTrey GmbH | Process for preparing a dental resin-modified glass ionomer composition |
| WO2018146958A1 (ja) | 2017-02-09 | 2018-08-16 | 富士フイルム株式会社 | ハーフミラー、ハーフミラーの製造方法、および画像表示機能付きミラー |
| EP3360532B1 (en) | 2017-02-13 | 2022-04-27 | Dentsply DeTrey GmbH | Dental composition |
| WO2018159236A1 (ja) | 2017-02-28 | 2018-09-07 | 富士フイルム株式会社 | インクジェット用液体組成物、及び、インクジェット記録方法 |
| KR102588712B1 (ko) | 2017-06-02 | 2023-10-17 | 코베스트로 (네덜란드) 비.브이. | 광섬유용의 내열성 방사선 경화성 코팅 |
| US10858527B2 (en) | 2017-07-19 | 2020-12-08 | Ricoh Company, Ltd. | Composition, cured product, image forming apparatus, and image forming method |
| EP3449895A1 (en) | 2017-08-30 | 2019-03-06 | Dentsply DeTrey GmbH | Photoinitiator modified polyacidic polymer |
| CN111050730B (zh) | 2017-08-30 | 2023-07-28 | 登特斯普伊德特雷有限公司 | 光引发剂改性的多元酸聚合物 |
| EP3449894A1 (en) | 2017-08-31 | 2019-03-06 | Dentsply DeTrey GmbH | Dental composition comprising a particulate carrier supporting a coinitiator |
| EP4312066A3 (en) | 2017-09-07 | 2024-04-17 | FUJIFILM Corporation | One-way mirror film for displaying projected images, laminated glass for displaying projected images, and image display system |
| CN111315701B (zh) | 2017-11-03 | 2022-10-14 | 科思创(荷兰)有限公司 | 包含用液体可辐射固化超吸收性聚合物组合物涂布的纤维的阻水体系 |
| CN111683640B (zh) | 2018-01-03 | 2023-10-27 | 登士柏希罗纳有限公司 | 牙科组合物 |
| EP3530259B1 (en) | 2018-02-22 | 2024-12-25 | Dentsply DeTrey GmbH | Dental composition |
| EP3757082B1 (en) | 2018-02-23 | 2024-05-01 | FUJIFILM Corporation | Method for manufacturing laminated glass for displaying image, laminated glass for displaying image, and image display system |
| EP3536304A1 (en) | 2018-03-07 | 2019-09-11 | Dentsply DeTrey GmbH | Dental impression material |
| EP3536303A1 (en) | 2018-03-07 | 2019-09-11 | Dentsply DeTrey GmbH | Dental composition |
| WO2019222586A1 (en) | 2018-05-18 | 2019-11-21 | Dentsply Sirona Inc. | Macromonomer based light-curable dental impression material |
| EP3632401A1 (en) | 2018-10-01 | 2020-04-08 | Dentsply Sirona Inc. | Macromonomer based light-curable dental impression material |
| JP7218385B2 (ja) | 2018-06-01 | 2023-02-06 | コベストロ (ネザーランズ) ビー.ヴィー. | 交互オリゴマーを介して光ファイバーをコーティングするための放射線硬化性組成物とそれから生成されたコーティング |
| US11964906B2 (en) | 2018-08-30 | 2024-04-23 | Covestro (Netherlands) B.V. | Radiation curable compositions for coating optical fiber |
| WO2020053723A1 (en) | 2018-09-14 | 2020-03-19 | 3M Innovative Properties Company | Composite materials including ceramic fibers and nanoclusters, dental products, kits, and methods of making and using same |
| WO2020080355A1 (ja) | 2018-10-17 | 2020-04-23 | 富士フイルム株式会社 | 投映像表示用部材、ウインドシールドガラスおよびヘッドアップディスプレイシステム |
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Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3826640A (en) * | 1971-08-10 | 1974-07-30 | Mobil Oil Corp | Substituted benzoylphosphonates as herbicides |
-
1978
- 1978-07-14 DE DE19782830927 patent/DE2830927A1/de not_active Withdrawn
-
1979
- 1979-07-13 JP JP8833679A patent/JPS5515471A/ja active Granted
- 1979-07-13 CA CA000331829A patent/CA1138877A/en not_active Expired
-
1980
- 1980-05-09 US US06/148,221 patent/US4324744A/en not_active Expired - Lifetime
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0057474A3 (en) * | 1979-03-14 | 1982-10-13 | Basf Aktiengesellschaft | Acylphosphine oxde compounds, their preparation and use |
| EP0047902A3 (en) * | 1980-09-15 | 1982-09-29 | Basf Aktiengesellschaft | Acylphosphinesulfide compounds, process for their preparation and their use |
| EP0062839A1 (de) * | 1981-04-09 | 1982-10-20 | BASF Aktiengesellschaft | Acylphosphinverbindungen und ihre Verwendung |
| US4447520A (en) * | 1981-08-24 | 1984-05-08 | Basf Aktiengesellschaft | Acylphosphine oxides and their use |
| DE3139984A1 (de) * | 1981-10-08 | 1983-04-28 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von acylphosphinoxiden |
| DE3443221A1 (de) * | 1984-11-27 | 1986-06-05 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Bisacylphosphinoxide, ihre herstellung und verwendung |
| DE4025386A1 (de) * | 1990-08-10 | 1992-02-27 | Herberts Gmbh | Verfahren zur haertung von radikalisch polymerisierbaren massen, ueberzuegen und druckfarben, neue carboxyphosphanoxide und deren verwendung als photoinitiatoren |
| US5750590A (en) * | 1995-02-22 | 1998-05-12 | Heraeus Kulzer Gmbh | Polymerizable material |
| US6114408A (en) * | 1998-02-06 | 2000-09-05 | American Dental Association Health Foundation | Single-solution adhesive resin formulations |
| EP2065890A2 (en) | 2007-11-30 | 2009-06-03 | FUJIFILM Corporation | Optical recording composition and holographic recording medium |
| WO2010110055A1 (ja) | 2009-03-23 | 2010-09-30 | 富士フイルム株式会社 | 接合型レンズ用硬化性樹脂組成物、撮像レンズ、及び、撮像レンズの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6340799B2 (cs) | 1988-08-12 |
| US4324744A (en) | 1982-04-13 |
| CA1138877A (en) | 1983-01-04 |
| JPS5515471A (en) | 1980-02-02 |
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| 8141 | Disposal/no request for examination |